Dimethylformamide → HCID 86630777, compound

HRID 238447Notes

Reaction equation

HRID 238447 reaction equation
CN(C=O)C.[N+:6]([C:9]1[CH:10]=[CH:11][C:12]([C:20]([F:26])([F:25])[C:21]([F:24])([F:23])[F:22])=[C:13]([CH:19]=1)[O:14][CH2:15][CH:16]1[CH2:18][O:17]1)([O-:8])=[O:7]>CCOC(C)=O>[N+:6]([C:9]1[CH:10]=[CH:11][C:12]([C:20]([F:26])([F:25])[C:21]([F:22])([F:23])[F:24])=[C:13]([CH:19]=1)[O:14][CH2:15][C@@H:16]1[CH2:18][O:17]1)([O-:8])=[O:7]

Participants

4

Reactant 2

HCID 6228DimethylformamideHCID 21959393HCID 21959393, compound

Product 1

HCID 86630777HCID 86630777, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Combined 5-nitro-2-pentafluoromethylphenol (2.69 g), DMF (25 ml) K2CO3 (3.03 g) and (S) toluene-4-sulfonic acid oxiranyl-methyl ester (2.27 g) and stirred the mixture at 90° C. After about 4 hours, the mix was cooled, diluted with EtOAc, washed with H2O, 1N NaOH (2×), 1N HCl and then with brine. Dried over Na2SO4, filtered and concentrated in vacuo. Purified the crude on silica gel column with 5% EtOAc/hexane and drying under high vacuum provided the (S)-2-(5-nitro-2-pentafluoroethyl-phenoxymethyl)-oxirane.

Workup

  1. temperaturethe mix was cooled
  2. washwashed with H2O, 1N NaOH (2×), 1N HCl
  3. dry with materialDried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurified the crude on silica gel column with 5% EtOAc/hexane
  7. customdrying under high vacuum

Sources & evidence

ORD record
ord-f8640c9bae114b2caca04290e6c791eb
Source dataset
uspto-grants-2014_02
Patent number
US08642624B2

Reaction notes

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